Winter Park Villas
Homes for Sale in Winter Park, FL
All 337 homes for sale in WINTER PARK, FL · median $664,900 · 70 homes for sale in 32792 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, Winter Park Villas in Winter Park, FL has 5 homes for sale, asking from $199,900 to $3,950,000 (median $1,595,000). Homes listed or recently sold were built 1925 - 2024; none of the 15 geocoded homes sit in a FEMA special flood hazard zone (median elevation 91 ft).
Homes For Sale Right Now in Winter Park Villas
Live MLS inventory for Winter Park Villas. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active · 174 daysTop listing
Active · 1 days
Active · 2 daysActive and pending Winter Park Villas listings as of 2026-09-12, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2016 through 2026. Tap any home to ask about it.
Winter Park Villas is a single-phase community built out in 1981, so every unit shares the same age and general construction profile. With only 102 homes total and just 2 active listings at this snapshot, supply here is thin by nature, not by market timing.
Months supply sits at 3.4, which reads as a balanced market, but that number is easy to overweight in a community this small. A single listing entering or leaving the pool can swing the ratio. Pricing here is going to be driven far more by unit condition and any updates to a 1981-era interior than by broad market momentum.
Winter Park Villas right now
🟡 Balanced market. 4.0 months of supply and 0% of the inventory already under contract put buyers and sellers on roughly even footing.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of September 12, 2026. Confidence: Low (4 active and pending listings, 1 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 15, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Winter Park Villas is a gated, deed-restricted community of 102 villa-style homes built in 1981, with a median living area of 1,037 square feet and shared amenities including a clubhouse, fitness center, pool, and tennis courts.
Stellar MLS sales records identify 25 homes in Winter Park Villas that have changed hands since 2006, built between 1981 and 1984 (median 1981), with a median living area of about 1,120 sq ft and a typical 2-bedroom, 2-bath layout; 80% are condominiums. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Flood zones in Winter Park Villas: of 15 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Winter Park.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
The setting & the homes.
Aerial and on-site photos of Winter Park Villas. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Winter Park VillasPhotos from Stellar MLS listings in Winter Park Villas; content deemed reliable but not guaranteed.
Who Winter Park Villas is best for.
Best for
- Buyers who want a low-maintenance, amenity-rich villa and are comfortable with a 1981-era interior that may need updating
- Investors evaluating a community with a notable share of non-owner-occupied units for potential rental use
- Buyers prioritizing a gated, deed-restricted setting with shared clubhouse, pool, and tennis access over square footage
Probably not for
- Buyers who need more than roughly 1,000 square feet of living space
- Buyers who want a wide pool of active listings to compare before making an offer
- Buyers uncomfortable with the maintenance and updating needs typical of a home built in 1981
The market around Winter Park Villas
Winter Park Villas is too small for its own price trend, so here is the market around it.
In ZIP 32792, 137 homes are on the market and 21% are under contract — a steady corner of Winter Park.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
In ZIP 32792 (WINTER PARK), 612 homes closed in the last 12 months at a median of $408K ($259/sq ft), down 2.0% year over year, with a median 28 days on market. Right now 48 active and 14 pending listings put supply at about 3.3 months - a balanced market. See the live ZIP 32792 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Winter Park Villas specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in WINTER PARK VILLAS, WINTER PARK
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
Winter Park Villas on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at Winter Park Villas
- Clubhouse · reported on 1 of 4 listings
- Fitness Center · reported on 1 of 4 listings
- Pool · reported on 1 of 4 listings
- Tennis Court(s) · reported on 1 of 4 listings
- Deed Restrictions · reported on 1 of 4 listings
- Security Gate · reported on 1 of 4 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Audubon Park K8 · Elementary
- Audubon Park K-8 · Middle
- Winter Park High · High
Zoned schools reflect the assignments reported on recent Winter Park Villas listings and can change; always confirm with Orange County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Winter Park Villas address.
Shop the zone: Homes zoned for Winter Park High High School
The Winter Park Villas buying strategy.
If we were buying in Winter Park Villas today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Winter Park Villas.
A small, single-era villa community
Every home in Winter Park Villas dates to 1981, which means buyers are largely choosing between units at similar ages rather than comparing older stock to newer construction. At a median of 1,037 square feet, these are compact, efficient floor plans consistent with an attached villa product rather than larger single-family footprints.
The homestead share here is notably low, at roughly 21%, which suggests a meaningful portion of the community is held as non-owner-occupied property - investment, rental, or seasonal use. That's a relevant data point for anyone weighing rental potential or expecting to buy alongside primarily owner-occupied neighbors. With only 2 active listings against 102 total homes, buyers should expect to move decisively when something in the right condition and price comes up, and sellers should know that pricing precedent is thin and highly sensitive to condition and updates.
The location and the amenities are priced into every listing in Winter Park Villas. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community this small, with only a handful of listings active at any time, the comps are limited and every unit's condition matters more than usual. We track this niche market closely enough to help you weigh a specific villa's finishes and updates against what has actually moved, rather than relying on broad Winter Park averages that don't reflect a 1981-built, deed-restricted community.
Winter Park Villas in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $451/month (about $5,412/yr) · median of 6 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $451 per month ($5,412 a year) - the median AssociationFee across 6 MLS records, normalised to a monthly figure; most are billed monthly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Winter Park Villas buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Winter Park Villas sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winter Park Villas, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Winter Park Villas home worth?
Get a no-obligation home value based on real comparable sales in Winter Park Villas, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Winter Park →
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Orange County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Orange County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
WINTER PARK VILLAS Market Scorecard
WINTER PARK VILLAS is currently a balanced market. About 4.0 months of supply, a median asking price of $1,295,500, and homes go under contract in about 14 days.
Typical home value in the 32789 ZIP is $809,773, about 61.9% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Frequently Asked Questions
Is Winter Park Villas a buyer's or seller's market right now?
Who is the best real estate agent for Winter Park Villas?
How do I find a top Winter Park real estate agent who knows Winter Park Villas?
Can Momentum Realty connect me with an agent for Winter Park Villas?
Should you buy in Winter Park Villas?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 12, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2016 (10 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
Looking to buy here? Search homes for sale →
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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Winter Park Villas fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Winter Park Villas with Momentum Realty’s local guides.